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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2428
https://doi.org/10.1107/S1600536810034057

2-(4-Meth­­oxy­phen­­oxy)-3-nitro­pyridine

Shah Bakhtiar Nasir,a Zanariah Abdullah,a‡ Zainal A. Fairuz,a Seik Weng Nga and Edward R. T. Tiekinka*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 August 2010; accepted 24 August 2010; online 28 August 2010)

In the title mol­ecule, C12H10N2O4, the pyridine and benzene rings are almost orthogonal [dihedral angle = 86.69 (11)°], with the pyridine N atom directed towards the centre of the benzene ring. The –NO2 [O—N—C—C = −26.1 (3)°] and –OMe [C—O—C—C = 166.5 (2)°] substituents are not coplanar with their respective aromatic rings. In the crystal, supra­molecular layers in the ab plane are formed via C—H⋯π inter­actions involving methyl H atoms and the pyridine and benzene rings. Short N—O⋯π contacts (where the π-system is derived from the pyridine ring) occur between layers in the c-axis direction.

Related literature

For background to fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001[Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.]); Abdullah (2005[Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.]). For a related structure, see: Nasir et al. (2010[Nasir, S. B., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2187.]).

[Scheme 1]

Experimental

Crystal data

  • C12H10N2O4

  • Mr = 246.22

  • Orthorhombic, P b c a

  • a = 7.4737 (10) Å

  • b = 12.8128 (17) Å

  • c = 24.529 (3) Å

  • V = 2348.8 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.30 × 0.28 × 0.07 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • 16986 measured reflections

  • 2066 independent reflections

  • 1364 reflections with I > 2σ(I)

  • Rint = 0.060
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.123

  • S = 1.03

  • 2066 reflections

  • 165 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,C1–C5 and C6–C11 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C12—H12a⋯Cg1i 0.96 2.73 3.521 (3) 140
C12—H12b⋯Cg2ii 0.96 2.80 3.616 (3) 143
N2—O1⋯Cg1iii 1.22 (1) 3.35 (1) 4.240 (2) 130 (1)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810034057/hb5614sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810034057/hb5614Isup2.hkl

checkCIF report


Comment top

Continued studies into the structural chemistry of N-heterocycle derivatives related to the title compound (Nasir et al., 2010) arise owing to interest in examining their fluorescence properties (Kawai et al. 2001; Abdullah, 2005). It was in this context that the synthesis and characterization of the title compound, (I), was investigated.

In (I), Fig. 1, the pyridine ring is orthogonal to the benzene ring [dihedral angle = 86.69 (11) °] and is orientated so that the pyridine-N atom is directed towards the centre of the benzene ring. Whereas the methoxy group is deviates from co-planarity with the benzene ring to which it is connected [the C12–O4–C9–C8 torsion angle = 166.5 (2) °], the nitro group is even further twisted out of the plane of the pyridine ring [O1–N2–C2–C1 = -26.1 (3) °].

In the crystal packing, C–H..π and N–O···π interactions contribute to the stabilization of the structure. The C–H..π interactions involve methyl-H atoms interacting with the pyridine and benzene rings, and lead to the formation of layers in the ab plane, Fig. 2 and Table 1. The layers stack along the c axis and are connected by N–O···π contacts, where the π system is derived from the pyridine ring, Fig. 3 and Table 1.

Related literature top

For background to fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005). For a related structure, see: Nasir et al. (2010).

Experimental top

4-Methoxyphenol (1.19 g, 96 mmol) was mixed with sodium hydroxide (0.384 g, 96 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloro-3-nitropyridine (1.49 g, 96 mmol) at 423–433 K for 5 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped colourless blocks of (I).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Uequiv(C).

Structure description top

Continued studies into the structural chemistry of N-heterocycle derivatives related to the title compound (Nasir et al., 2010) arise owing to interest in examining their fluorescence properties (Kawai et al. 2001; Abdullah, 2005). It was in this context that the synthesis and characterization of the title compound, (I), was investigated.

In (I), Fig. 1, the pyridine ring is orthogonal to the benzene ring [dihedral angle = 86.69 (11) °] and is orientated so that the pyridine-N atom is directed towards the centre of the benzene ring. Whereas the methoxy group is deviates from co-planarity with the benzene ring to which it is connected [the C12–O4–C9–C8 torsion angle = 166.5 (2) °], the nitro group is even further twisted out of the plane of the pyridine ring [O1–N2–C2–C1 = -26.1 (3) °].

In the crystal packing, C–H..π and N–O···π interactions contribute to the stabilization of the structure. The C–H..π interactions involve methyl-H atoms interacting with the pyridine and benzene rings, and lead to the formation of layers in the ab plane, Fig. 2 and Table 1. The layers stack along the c axis and are connected by N–O···π contacts, where the π system is derived from the pyridine ring, Fig. 3 and Table 1.

For background to fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005). For a related structure, see: Nasir et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. Supramolecular layer in the ab plane mediated by C–H···π interactions, shown as purple dashed lines, in the structure of (I).
[Figure 3] Fig. 3. Unit-cell contents shown in projection down the a axis in (I), highlighting the stacking of layers along the c direction. The C–H···π and N–O···π interactions are shown as purple and orange dashed lines, respectively.
2-(4-Methoxyphenoxy)-3-nitropyridine top
Crystal data top
C12H10N2O4F(000) = 1024
Mr = 246.22Dx = 1.393 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2051 reflections
a = 7.4737 (10) Åθ = 3.2–20.1°
b = 12.8128 (17) ŵ = 0.11 mm−1
c = 24.529 (3) ÅT = 293 K
V = 2348.8 (5) Å3Block, colourless
Z = 80.30 × 0.28 × 0.07 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		1364 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = −8→8
16986 measured reflectionsk = −15→15
2066 independent reflectionsl = −27→29
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.4422P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2066 reflectionsΔρmax = 0.19 e Å−3
165 parametersΔρmin = −0.17 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0042 (9)
Crystal data top
C12H10N2O4V = 2348.8 (5) Å3
Mr = 246.22Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.4737 (10) ŵ = 0.11 mm−1
b = 12.8128 (17) ÅT = 293 K
c = 24.529 (3) Å0.30 × 0.28 × 0.07 mm
Data collection top
Bruker SMART APEX CCD
diffractometer		1364 reflections with I > 2σ(I)
16986 measured reflectionsRint = 0.060
2066 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.03Δρmax = 0.19 e Å−3
2066 reflectionsΔρmin = −0.17 e Å−3
165 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6185 (3)0.61280 (14)0.47253 (8)0.0772 (6)
O20.4138 (3)0.73025 (14)0.47339 (9)0.0986 (7)
O30.56918 (18)0.47091 (11)0.39640 (7)0.0603 (5)
O40.8030 (2)0.16173 (11)0.25569 (7)0.0659 (5)
N10.2758 (2)0.42013 (14)0.38381 (8)0.0536 (5)
N20.4665 (3)0.64262 (14)0.46264 (8)0.0553 (5)
C10.3912 (3)0.48503 (15)0.40591 (9)0.0440 (5)
C20.3378 (3)0.57022 (15)0.43811 (8)0.0450 (5)
C30.1573 (3)0.58629 (19)0.44736 (9)0.0578 (6)
H30.11810.64240.46820.069*
C40.0362 (3)0.5166 (2)0.42471 (11)0.0654 (7)
H4−0.08610.52450.43030.078*
C50.1010 (3)0.4359 (2)0.39382 (10)0.0607 (6)
H50.01920.38920.37890.073*
C60.6196 (3)0.39115 (16)0.35921 (10)0.0473 (6)
C70.6735 (3)0.29624 (17)0.37948 (9)0.0518 (6)
H70.66840.28260.41670.062*
C80.7358 (3)0.22109 (16)0.34344 (9)0.0521 (6)
H80.77390.15670.35660.063*
C90.7416 (3)0.24148 (15)0.28798 (9)0.0478 (6)
C100.6896 (3)0.33849 (16)0.26848 (10)0.0557 (6)
H100.69600.35310.23140.067*
C110.6281 (3)0.41331 (16)0.30457 (10)0.0556 (6)
H110.59260.47840.29180.067*
C120.7750 (4)0.1697 (2)0.19822 (10)0.0708 (8)
H12A0.81730.10740.18070.106*
H12B0.83930.22890.18430.106*
H12C0.64960.17830.19100.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0679 (12)0.0787 (13)0.0851 (14)0.0010 (10)−0.0152 (10)−0.0238 (10)
O20.1079 (17)0.0574 (11)0.1304 (18)0.0146 (11)−0.0116 (14)−0.0361 (11)
O30.0388 (9)0.0600 (9)0.0822 (12)−0.0012 (7)0.0057 (8)−0.0320 (8)
O40.0852 (14)0.0505 (9)0.0620 (11)0.0161 (8)0.0111 (9)−0.0123 (8)
N10.0424 (11)0.0514 (11)0.0669 (13)−0.0061 (9)0.0038 (9)−0.0059 (9)
N20.0690 (14)0.0490 (11)0.0478 (12)0.0041 (10)0.0011 (10)−0.0068 (9)
C10.0413 (12)0.0424 (11)0.0483 (13)0.0008 (9)0.0061 (10)−0.0011 (9)
C20.0500 (13)0.0437 (11)0.0414 (12)0.0054 (10)0.0039 (10)0.0027 (9)
C30.0606 (16)0.0626 (14)0.0503 (14)0.0187 (13)0.0118 (12)0.0007 (11)
C40.0432 (14)0.0796 (18)0.0733 (18)0.0092 (13)0.0110 (13)0.0079 (14)
C50.0426 (13)0.0678 (15)0.0717 (17)−0.0073 (12)0.0027 (12)0.0039 (13)
C60.0353 (11)0.0450 (12)0.0616 (15)−0.0023 (9)0.0046 (10)−0.0141 (10)
C70.0469 (13)0.0571 (13)0.0514 (14)−0.0012 (10)0.0048 (11)−0.0043 (11)
C80.0534 (14)0.0427 (11)0.0604 (15)0.0064 (10)0.0017 (12)0.0002 (11)
C90.0470 (13)0.0431 (11)0.0533 (14)0.0015 (10)0.0057 (11)−0.0051 (10)
C100.0661 (16)0.0468 (12)0.0540 (15)0.0027 (11)0.0072 (12)0.0020 (10)
C110.0587 (15)0.0386 (11)0.0694 (17)0.0041 (10)0.0021 (13)−0.0019 (11)
C120.0761 (19)0.0777 (17)0.0585 (17)0.0018 (14)0.0073 (14)−0.0230 (13)
Geometric parameters (Å, º) top
O1—N21.223 (2)C5—H50.9300
O2—N21.219 (2)C6—C111.371 (3)
O3—C11.363 (3)C6—C71.374 (3)
O3—C61.421 (2)C7—C81.388 (3)
O4—C91.372 (2)C7—H70.9300
O4—C121.429 (3)C8—C91.386 (3)
N1—C11.315 (3)C8—H80.9300
N1—C51.345 (3)C9—C101.387 (3)
N2—C21.466 (3)C10—C111.384 (3)
C1—C21.405 (3)C10—H100.9300
C2—C31.383 (3)C11—H110.9300
C3—C41.387 (3)C12—H12A0.9600
C3—H30.9300C12—H12B0.9600
C4—C51.371 (3)C12—H12C0.9600
C4—H40.9300
C1—O3—C6117.66 (15)C7—C6—O3118.8 (2)
C9—O4—C12117.84 (18)C6—C7—C8118.8 (2)
C1—N1—C5117.85 (19)C6—C7—H7120.6
O2—N2—O1123.0 (2)C8—C7—H7120.6
O2—N2—C2117.4 (2)C7—C8—C9120.3 (2)
O1—N2—C2119.57 (18)C7—C8—H8119.8
N1—C1—O3119.05 (18)C9—C8—H8119.8
N1—C1—C2122.5 (2)O4—C9—C10124.2 (2)
O3—C1—C2118.47 (18)O4—C9—C8115.89 (19)
C3—C2—C1119.0 (2)C10—C9—C8119.90 (19)
C3—C2—N2118.59 (19)C11—C10—C9119.6 (2)
C1—C2—N2122.40 (19)C11—C10—H10120.2
C2—C3—C4118.3 (2)C9—C10—H10120.2
C2—C3—H3120.8C6—C11—C10119.8 (2)
C4—C3—H3120.8C6—C11—H11120.1
C5—C4—C3118.5 (2)C10—C11—H11120.1
C5—C4—H4120.8O4—C12—H12A109.5
C3—C4—H4120.8O4—C12—H12B109.5
N1—C5—C4123.9 (2)H12A—C12—H12B109.5
N1—C5—H5118.1O4—C12—H12C109.5
C4—C5—H5118.1H12A—C12—H12C109.5
C11—C6—C7121.54 (19)H12B—C12—H12C109.5
C11—C6—O3119.39 (19)
C5—N1—C1—O3−180.0 (2)C3—C4—C5—N1−0.3 (4)
C5—N1—C1—C2−1.4 (3)C1—O3—C6—C1186.8 (2)
C6—O3—C1—N15.0 (3)C1—O3—C6—C7−98.8 (2)
C6—O3—C1—C2−173.55 (19)C11—C6—C7—C8−0.8 (3)
N1—C1—C2—C30.5 (3)O3—C6—C7—C8−175.10 (18)
O3—C1—C2—C3179.02 (19)C6—C7—C8—C9−0.6 (3)
N1—C1—C2—N2−179.89 (19)C12—O4—C9—C10−14.5 (3)
O3—C1—C2—N2−1.4 (3)C12—O4—C9—C8166.5 (2)
O2—N2—C2—C3−24.8 (3)C7—C8—C9—O4−179.2 (2)
O1—N2—C2—C3153.5 (2)C7—C8—C9—C101.8 (3)
O2—N2—C2—C1155.6 (2)O4—C9—C10—C11179.4 (2)
O1—N2—C2—C1−26.1 (3)C8—C9—C10—C11−1.6 (3)
C1—C2—C3—C40.6 (3)C7—C6—C11—C101.0 (3)
N2—C2—C3—C4−179.1 (2)O3—C6—C11—C10175.26 (19)
C2—C3—C4—C5−0.6 (4)C9—C10—C11—C60.2 (4)
C1—N1—C5—C41.4 (4)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1,C1–C5 and C6–C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12a···Cg1i0.962.733.521 (3)140
C12—H12b···Cg2ii0.962.803.616 (3)143
N2—O1···Cg1iii1.22 (1)3.35 (1)4.240 (2)130 (1)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1/2, y, −z+1/2; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC12H10N2O4
Mr246.22
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)7.4737 (10), 12.8128 (17), 24.529 (3)
V (Å3)2348.8 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.30 × 0.28 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		16986, 2066, 1364
Rint0.060
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.123, 1.03
No. of reflections2066
No. of parameters165
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.17

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the N1,C1–C5 and C6–C11 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C12—H12a···Cg1i0.962.733.521 (3)140
C12—H12b···Cg2ii0.962.803.616 (3)143
N2—O1···Cg1iii1.223 (2)3.350 (2)4.240 (2)129.93 (15)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1/2, y, −z+1/2; (iii) −x+1, −y+1, −z+1.
 

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

AZ thanks the Ministry of Higher Education, Malaysia, for research grants (PS341/2010, FP047/2008 C and RG027/09AFR). The authors are also grateful to the University of Malaya for support of the crystallographic facility.

References

First citationAbdullah, Z. (2005). Int. J. Chem. Sci. 3, 9–15.  CAS Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2428
https://doi.org/10.1107/S1600536810034057
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